Oxalic Acid → HCID 15480258, compound

HRID 582725Notes

Reaction equation

HRID 582725 reaction equation
[NH2:1][C:2]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(O)(=O)[C:19](O)=[O:20]>C(OCC)(=O)C.C(O)C>[OH-:9].[NH4+:1].[CH3:19][OH:20].[NH2:1][C:2]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 971Oxalic AcidHCID 15480258HCID 15480258, compound

Product 2

HCID 15480258HCID 15480258, compoundYield 148.8%HCID 21894508Ammonium hydroxide methanolYield 5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compounds prepared as described in Example 2 (20.71 g) in ethyl acetate (200 mL) was treated with a solution of oxalic acid (15.46 g) in ethanol (50 mL). The resulting mixture was stirred at room temperature. After one hour, the reaction mixture was treated with additional ethanol (50 mL). After 18 hours, the mixture was filtered, and the filtrate was evaporated to dryness in vacuo. The residue was treated with 1 N sodium hydroxide, and the resulting mixture extracted with diethyl ether. The combined ether extracts were washed with brine, dried over potassium carbonate, filtered, and concentrated in vacuo. The residue was purified by silica-gel chromatography, eluting with methylene chloride:5% ammonium hydroxide/methanol (97:3), to give 15.41 g of the title compound.

Workup

  1. customA solution of the compounds prepared
  2. waitAfter 18 hours
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated to dryness in vacuo
  5. additionThe residue was treated with 1 N sodium hydroxide
  6. extractionthe resulting mixture extracted with diethyl ether
  7. washThe combined ether extracts were washed with brine
  8. dry with materialdried over potassium carbonate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica-gel chromatography
  12. washeluting with methylene chloride

Sources & evidence

ORD record
ord-9932a13ec8fe4a45b85ade1bc9868578
Source dataset
uspto-grants-1999_07
Patent number
US05925680

Reaction notes

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